Steve Jobs founded Apple and changed the way we think about technology. Richard Branson founded the Virgin Group, which started as a record label and now includes more than 58 companies around the world.

They’re two of the most famous entrepreneurs of the century — and according to Alexa Clay and Kyra Maya Phillips, that’s because the share the same “hybrid DNA.” They’re a special breed of innovator: they’re misfit entrepreneurs.

As Clay and Phillips explain in their book, “The Misfit Economy,” that’s not necessarily a common cocktail.

Misfits and entrepreneurs do share some traits, but they shouldn’t be conflated. Both groups are “natural risk takers who pursue freedom and autonomy through their own passion and hustle.”

But there’s more to being a misfit than hustle and passion.

In Clay’s and Phillips’ analysis, misfits stand out because they’re “countercultural, self-questioning, and vulnerable. They push boundaries. They challenge systems.”

It’s a rare combination — plenty of entrepreneurs fit in all too well, and lots of misfits aren’t up for playing so close to mainstream society’s rules. But when “a misfit personality finds herself in the body of an entrepreneur, and when these identities merge, the results can be explosive,” they write.
And for evidence, we need look no further than Jobs and Branson.

Steve Jobs was confident, he was a risk-taker, he was “achievement-oriented,” and he cared about winning over others. And had that been all he was, he still might have been a wildly successful entrepreneur.

But that isn’t all he was: he was also a misfit. To see his vulnerability, all you need to do is rewatch hislegendary Stanford commencement speech. And it’s no accident that Apple’s most famous ad began “Here’s to the crazy ones. The misfits. The rebels. The troublemakers. The round pegs in the square holes.” (In fact, the montage for that ad featured none other than Sir Richard Branson, the the version below — narrated by Jobs — never aired.)

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Jobs was able to encourage what Clay and Phillips describe as an “alternative, renegade spirit” at Apple — and to do it at a time when the tech industry full of “buttoned-down” organisations — because of he was a misfit.

Richard Branson is hardly a Jobs doppelgänger, but his success, the authors argue, is due to that same “maverick blend.” His misfit status allowed pursued avenues that other people were “too afraid” to consider — and he continues to do so. (Exhibit A: Virgin’s play for the space tourism market.)

In interviews, Branson has said as much himself, arguing his dyslexia has proved one of his greatest assets. Having a different way of processing language made him think differently, he’s explained — and it’s that ability that’s helped him to go beyond the bounds of “normal,” to be, per the Apple ad, a “round peg in a square hole.”